Sodium Sulfite → N-(6phenylhexyl)-4-benzylsulphinyl-2-oxoazetidin-1-yl acetamide

HRID 1603649Notes

Reaction equation

HRID 1603649 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:29])[CH2:15][N:16]2[CH:19]([S:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:18][C:17]2=[O:28])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:38])C=1.S([O-])([O-])=O.[Na+].[Na+].C(=O)([O-])O.[Na+]>ClCCl>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:29])[CH2:15][N:16]2[CH:19]([S:20]([CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:38])[CH2:18][C:17]2=[O:28])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 19605281N-(6-phenylhexyl)-(4-benzylthio-2-oxoazetidin-1-yl)acetamide

Product 1

HCID 11750677N-(6phenylhexyl)-4-benzylsulphinyl-2-oxoazetidin-1-yl acetamideYield 20.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of N-(6-phenylhexyl)-4-benzylthio-2-oxoazetidin-1-yl acetamide (18.0 g, 43.8 mmol) in dichloromethane (500 ml) was cooled to -70° C. and a solution of m-chloroperbenzoic acid (6.7 g, 43.8 mmol) in dichloromethane (500 ml) added dropwise with stirring over 60 min. After a further 3 h at -60° C., the reaction mixture was shaken with a mixture of saturated aqueous sodium sulphite and saturated sodium hydrogen carbonate. The organic layer was separated, washed with brine, dried (MgSO4) and evaporated to a solid which was titurated with ether and filtered. Two recrystallisations from ethyl acetate gave (4R,SR/4S,SS) N-(6phenylhexyl)-4-benzylsulphinyl-2-oxoazetidin-1-yl acetamide (3.8 g, 20%) mp 138-140° C.

Workup

  1. waitAfter a further 3 h at -60° C.
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated to a solid which
  6. filtrationfiltered
  7. customTwo recrystallisations from ethyl acetate

Sources & evidence

ORD record
ord-6ec0ca0ed321484ab3b5154676af61bd
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

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